I experience the issue myself as well, every once in a while. Tried CC cleaner to clean up registry and everything -- also keep in mind this repair PST file without data loss is a fairly recent reinstall of windows. I am unable to stay signed in to my work account on Teams, Outlook, Office365 for more than 5 minutes.

Outlook credential prompt loop

In the instances that this occurs the effected user is not new to MFA but has been running it for at least months. The problem appears to randomly affect users (I’ve had it affect myself once too), and the only solution appears to one of (or a combination of) the options in the OP. Out of 140 staff the problem seems to occur once every 2-3 weeks on average. In this case are you saying that there is a password prompt for the users credentials? Clear the Windows Credential manager or recreate the users Outlook profile. In fact if you just turned on MFA and you were not using MFA before you usually end up having to rebuild FixTechGuide support for Office 365 the profile and clearing the credential manager.

Loop of 'Sign in to your account'.

We had the issue where Outlook 2016 kept prompting for a password for an Office 365 user whose laptop was connected to their Office 365 account using Windows 10 Pro. The repeated issue logging in started after I enabled the modern authentication in the Office 365 administration panel. The user could use the Windows mail and calendar apps but Outlook wouldn’t connect and kept prompting for a password. Checking the Account in Word showed the correct authentication and subscription.

Resetting the Windows Credential Manager:

When we opened the old, existing profile it didn’t ask for ANY authentication, it just started working. Office 2016 is already Modern Authentication aware so APP passwords are not required. Native IOS and Android Mail apps will require the APP password or users can use Outlook for IOS/Android which is Modern Auth aware. FYI outlook 2013 requires a registry setting to work with MA. Where I work, we have a new sandbox tenant to make tests before rebuild Outlook data file quickly official deployment. I tried registering the account to my Outlook Desktop app and for some reason I am in a credential prompt loop that always asks for it anytime I input my password.

• It’s not caused by an out of sync MFA prompt as I have personally looked at a number of cases with the user as stepped through it.
• Problem doesn’t just happen on PC’s connected to the internal network, but can happen when a laptop is remote and connected via external wifi or mobile hotspot.
• Not sure if it has to do with being an onmicrosoft.com account that has no domain assigned to it.
• Checking the Account in Word showed the correct authentication and subscription.
• Office 2016 is already Modern Authentication aware so APP passwords are not required.
• Native IOS and Android Mail apps will require the APP password or users can use Outlook for IOS/Android which is Modern Auth aware.

Changing Outlook Security Settings:

Hi, my office 365 account used to work with my desktop apps, I have confirmed with my admin system twice already that I have the appropriate license and everything is enabled but i keep getting stuck in this loop. We are looking at using conditional access policies where a user with a Domain joined PC is not prompted for MFA. Right now we have it set to prompt when a user is not on any of our corporate networks or they are using a mobile device. The user had Office 2015 and Office 2016 credentials and Teams credentials that we deleted. We checked with Word that the account was connected–it was and the we opened Outlook and it immediately connected. We too have been seeing this more and more, all W10 on O365, although we use Okta as our MFA.